2-(4-氯苯氧基)-N-甲氧基-N-甲基乙酰胺 | 18232-70-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-(4-氯苯氧基)-N-甲氧基-N-甲基乙酰胺
• 英文名称: N-methoxy-2-(4-chloro-phenoxy)-N-methyl-acetamide
• 英文别名: 2-(4-chlorophenoxy)-N-methoxy-N-methylacetamide
• CAS: 18232-70-7
• 化学式: C₁₀H₁₂ClNO₃
• mdl: MFCD14707539
• 分子量: 229.663
• InChiKey: BZMCWLGUXMFYNU-UHFFFAOYSA-N

物化性质

• 熔点：
  52-53 °C
• 沸点：
  311.1±48.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-氯苯氧基)-N-甲氧基-N-甲基乙酰胺 在 Schwartz's reagent 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以82%的产率得到p-chlorophenoxyacetaldehyde
  参考文献：
  名称：

  Mild and Selective Hydrozirconation of Amides to Aldehydes Using Cp₂Zr(H)Cl:  Scope and Mechanistic Insight

  摘要：

  An investigation of the use of Cp2Zr(H)Cl (Schwartz's reagent) to reduce a variety of amides to the corresponding aldehydes under very mild reaction conditions and in high yields is reported. A range of tertiary amides, including Weinreb's amides, can be converted directly to the corresponding aldehydes with remarkable chemoselectivity. Primary and secondary amides proved to be viable substrates for reduction as well, although the yields were somewhat diminished as compared to the corresponding tertiary amides. Results from NMR experiments suggested the presence of a stable, 18-electron zirconacycle intermediate that presumably affords the aldehyde upon water or silica gel workup. A series of competition experiments revealed a preference of the reagent for substrates in which the lone pair of the nitrogen is electron releasing and thus more delocalized across the amide bond by resonance. This trend accounts for the observed excellent selectivity for tertiary amides versus esters. Experiments regarding the solvent dependence of the reaction suggested a kinetic profile similar to that postulated for the hydrozirconation of alkenes and alkynes. Addition of p-anisidine to the reaction intermediate resulted in the formation of the corresponding imine mimicking the addition of water that forms the aldehyde.

  DOI：

  10.1021/ja066362+
• 作为产物：
  描述：

  对氯苯氧乙酸 、 二甲羟胺盐酸盐 在 N,N'-羰基二咪唑 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到2-(4-氯苯氧基)-N-甲氧基-N-甲基乙酰胺
  参考文献：
  名称：

  Expedient Synthesis of 3-Alkoxymethyl- and 3-Aminomethyl-Pyrazolo[3,4-b]pyridines

  摘要：

  An effective strategy has been developed for the preparation of 3-alkoxymethyl-pyrazolo[3,4-b]pyridines, compounds that are currently not readily accessible by existing synthetic methods. Further manipulation of these compounds allows for access to 3-alkoxymethyl-pyrazolo[3,4-b]pyridines with a variety of substitution patterns as well as 3-aminomethyl-pyrazolo[3,4-b]pyridines.

  DOI：

  10.1021/jo802363q

文献信息

• Benzylamine analogues
  申请人：SANKYO COMPANY, LIMITED

  公开号：US20040067981A1

  公开（公告）日：2004-04-08

  A compound of the formula (I): 1 wherein R 1 represents C 1 -C 6 alkyl, amino (C 1 -C 6 alkyl)amino, di(C 1 -C 6 alkyl) amino or a nitrogen-containing saturated heterocyclic; R 2 and R 3 are the same or different and represent hydrogen or C 1 -C 6 alkyl; R a represents C 1 -C 6 alkyl or C 2 -C 6 alkenyl or together with R 2 represents a C 1 -C 3 alkylene; Arom represents aryl or heteroaryl; A represents a C 1 -C 6 alkylene; E represents a single bond, oxygen, sulfur or R 4 NR 4 —, wherein R 4 is hydrogen or C 1 -C 7 alkenoyl; X 1 and X 2 are the same or different and represent oxygen or sulfur; or a pharmacologically acceptable salt or ester thereof. The compound has superior acetylcholinesterase inhibitory action and selective serotonin reuptake inhibitory action, and is useful for treating or preventing Alzheimer's disease, depression, Huntington's chorea, Pick's disease, tardive dyskinesia, compulsive disorders or panic disorders.

  化合物的化学式为（I）：1，其中R1代表C1-C6烷基，氨基（C1-C6烷基）氨基，二（C1-C6烷基）氨基或含氮饱和杂环；R2和R3相同或不同，代表氢或C1-C6烷基；R代表C1-C6烷基或C2-C6烯基或与R2一起代表C1-C3烷基；Arom代表芳基或杂芳基；A代表C1-C6烷基；E代表单键，氧，硫或R4NR4—，其中R4为氢或C1-C7烯酰基；X1和X2相同或不同，代表氧或硫；或其药学上可接受的盐或酯。该化合物具有优异的乙酰胆碱酯酶抑制作用和选择性5-羟色胺再摄取抑制作用，并可用于治疗或预防阿尔茨海默病、抑郁症、亨廷顿舞蹈症、皮克病、迟发性运动障碍、强迫性障碍或惊恐障碍。
• BENZYLAMINE ANALOGUE
  申请人：BTG INTERNATIONAL LIMITED

  公开号：EP1362844B1

  公开（公告）日：2007-12-05
• US7504437B2
  申请人：——

  公开号：US7504437B2

  公开（公告）日：2009-03-17
• US7504393B2
  申请人：——

  公开号：US7504393B2

  公开（公告）日：2009-03-17
• US7514475B2
  申请人：——

  公开号：US7514475B2

  公开（公告）日：2009-04-07